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Guesthouse vacation rentals in Southside, Jacksonville

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Popular amenities for Southside, Jacksonville guesthouse rentals

Family-friendly guest house rentals

A colorful entrance leads into a wooden playground surrounded by a safety fence. The structure includes multiple towers and slides, providing ample play opportunities. Lush green grass is visible in the surrounding area, establishing a welcoming environment for children.
Guesthouse in Beaches
4.71 out of 5 average rating, 212 reviews

Cozy Cottage Studio, Walk to Beach

LaraRating, 5 stars10 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 favorite
The living area features a sectional couch in a neutral tone, complemented by a soft area rug. A modern kitchen with a white island and bar seating is visible, and natural light fills the space through windows adorned with plantation shutters.
Private room in Ponte Vedra Beach
4.97 out of 5 average rating, 105 reviews

Private Beach Access - Charming Villa

CameronRating, 5 stars1 day ago
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!
Top guest favorite
The kitchen features white cabinetry with ample storage and a spacious countertop. Stainless steel appliances, including a double oven and dishwasher, are visible. A window allows natural light to illuminate the workspace, and a small area rug adds a touch of warmth.
Guesthouse in Southeast Jacksonville
4.98 out of 5 average rating, 372 reviews

Private Apartment

EmilyRating, 5 stars2 weeks ago
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!
Guest favorite
A two-story pool house features a light blue exterior, complemented by a covered porch with four white rocking chairs. A paved pathway leads to the pool area, framed by greenery and trees. Stairs are visible on one side, providing access to the upper level.
Guesthouse in Jacksonville
4.74 out of 5 average rating, 450 reviews

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

KileyRating, 5 stars1 month ago
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!
Top guest favorite
The living area features a modern sofa adorned with plush cushions, complemented by a bright yellow side table. A stylish red refrigerator adds a pop of color, while natural light filters through window coverings. A flat-screen television is situated atop a sleek media console.
Guesthouse in Springfield
5 out of 5 average rating, 30 reviews

Lovely Guesthouse in the Up-and-Coming Springfield

CarolRating, 5 stars4 weeks ago
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

Superhost
A cozy sleeping area features a spacious bed with a soft white blanket. The room includes a kitchenette with modern appliances and a mounted television displaying a serene beach scene. Natural light enters through a window, enhancing the comfortably designed space.
Guesthouse in Jacksonville
4.8 out of 5 average rating, 50 reviews

The Little House

SherryRating, 5 stars3 weeks ago
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!!!
Guest favorite
Guesthouse in Southwest Jacksonville
4.93 out of 5 average rating, 190 reviews

Adorable 2 Bedroom Cottage

RichardRating, 5 stars3 weeks ago
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.
Top guest favorite
Guesthouse in St. Augustine
5 out of 5 average rating, 89 reviews

Comfortable and Gently Disney.

VillagomezRating, 5 stars3 days ago
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!!
Top guest favorite
A spacious patio features a comfortable seating area arranged with a wicker sofa and two matching chairs, each adorned with plush cushions. A round fire pit sits centrally, surrounded by patterned stone flooring. Natural light filters in from nearby windows.
Guesthouse in Southeast Jacksonville
4.97 out of 5 average rating, 72 reviews

Transforms, Full Kitchen/bath, Centrally located

GinoryRating, 5 stars3 days ago
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.
Top guest favorite
The entrance of a red wooden guest house is framed by lush greenery. A bright yellow door is centered between two large windows, while a welcoming doormat adds charm. The structure is complemented by a white column and features a cozy, inviting porch area.
Guesthouse in Avondale
5 out of 5 average rating, 31 reviews

Boone Park Studio

PhilipRating, 5 stars2 weeks ago
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!
Top guest favorite
Two modern seating areas are arranged in a bright, open space. Each chair features a dark upholstery with light-colored throw pillows. A decorative console table with a wheel design sits between the chairs, complemented by a sign that promotes a positive message.
Guesthouse in Jacksonville
4.99 out of 5 average rating, 85 reviews

Farmhouse luxury, you'll never want to leave

BenjaminRating, 5 stars1 month ago
Great host, beautiful property we enjoyed our stay!!
Guest favorite
A modern outdoor area features a round table with four green chairs, surrounded by gravel and greenery. A raised planter box displays various plants, while a small building with large glass doors complements the peaceful setting, enclosed by a wooden fence.
Guesthouse in Murray Hill
4.9 out of 5 average rating, 301 reviews

The Moody Loft (Murray Hill)

DollieRating, 5 stars2 weeks ago
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!!
Guest favorite
Guesthouse in Riverside
4.9 out of 5 average rating, 144 reviews

Charming Avondale Backhouse - King Bed!

AshleyRating, 5 stars2 weeks ago
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

Guest favorite
Guesthouse in Springfield
4.9 out of 5 average rating, 284 reviews

Downtown Jacksonville Historic District

TyneikaRating, 5 stars2 weeks ago
Directions were very clear, home looked nice and matched the description! Hosts had great communication
Top guest favorite
A view of an inviting pool area features a turquoise pool with a raised spa surrounded by a paved patio. Two thatched umbrellas provide shade over lounge chairs. Lush greenery is visible in the background, enhancing the serene setting. A small dog rests on a mat in the foreground.
Guesthouse in Ponte Vedra Beach
4.89 out of 5 average rating, 75 reviews

Palm Valley Pool House

JeanRating, 5 stars3 weeks ago
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. 😊
Top guest favorite
A modern kitchen features dark cabinetry and a green countertop. A stainless steel refrigerator stands prominently, while glass-door cabinets display decorative items. Natural light enters through a window, illuminating the space. A patterned rug adds warmth to the herringbone tile floor.
Guesthouse in Riverside
4.97 out of 5 average rating, 353 reviews

Henry’s Pad

BriaRating, 5 stars1 day ago
This was a very beautiful home, it gives villa vibes and very beautiful neighborhood! Thank you for such a beautiful stay!
Guest favorite
Guesthouse in Green Cove Springs
4.87 out of 5 average rating, 39 reviews

Country home

HaileyRating, 5 stars1 month ago
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!
Guest favorite
The modern kitchen features a large island with seating for four, accented by sleek gray bar stools. New stainless steel appliances include a refrigerator and stove, surrounded by light cabinetry and elegant countertops. Colorful artwork adorns the walls, adding a vibrant touch to the space.
Guesthouse in Murray Hill
4.91 out of 5 average rating, 238 reviews

Large 1 bedroom Cottage with full kitchen

BenRating, 5 stars1 week ago
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!
Top guest favorite
The image showcases the exterior entrance of the bungalow, featuring a wooden pathway leading to the house. A wooden fence with heart-shaped accents encloses the area, surrounded by pebbles and greenery. The white exterior of the bungalow contrasts with the natural tones of the landscaping.
Guesthouse in Avondale
4.98 out of 5 average rating, 152 reviews

Stylish Bungalow Near Dining,Parks & Entertainment

LeighRating, 5 stars1 week ago
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.
Top guest favorite
A bright bedroom is framed by double French doors with green trim. A spacious bed, featuring soft white linens and colorful accent pillows, occupies the center. Natural light enters through large windows adorned with bamboo shades, complementing the warm wooden floors and light-colored walls.
Guesthouse in Murray Hill
5 out of 5 average rating, 114 reviews

Hip + Modern Florida Hideaway

MichelleRating, 5 stars3 weeks ago
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.
Guest favorite
An aerial view captures a clear blue saltwater pool surrounded by a stone patio. Sun loungers and a shaded seating area with a table and umbrella are positioned nearby. Lush greenery from surrounding trees adds a natural ambiance to the space.
Guesthouse in Springfield
4.96 out of 5 average rating, 108 reviews

Spacious 2/1 in historic walkable neighborhood

BrittanyRating, 5 stars1 week ago
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

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  4. Duval County
  5. Jacksonville
  6. Southside
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