Best Vacation Homes in Southside
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
10.0- Balcony/Terrace
View
Pet Friendly- Parking
10.0- Fireplace/Heating
Pool- Kitchen
- Parking
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
10.0- Pet Friendly
- Parking
- Air Conditioner
- Internet
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
10.0- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
Southside Luxury Rentals
9.4- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
- Pet Friendly
- Parking
- Air Conditioner
- Child Friendly
10.0
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
8.4- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
7.8
Oceanfront- Hot Tub
- Fireplace/Heating
- Pool
10.0
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
8.6- Oceanfront
- Fireplace/Heating
- Pool
Ocean View
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
Southside Pet Friendly Vacation Rentals
10.0- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
10.0- Pet Friendly
- Parking
- Air Conditioner
- Internet
8.6- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
10.0- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
10.0- Pet Friendly
- Parking
- Air Conditioner
- Internet
10.0- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
10.0- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
10.0- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
Southside Large Vacation Homes
10.0- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
10.0- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
10.0- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
9.7- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
10.0- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
10.0- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
9.8- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
9.6- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
Why Choose Rent By Owner for your Southside Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Southside Vacation Rentals
Where are the best neighborhoods to stay in Southside?
Discover the vibrant neighborhoods of Southside in Jacksonville, Florida, where you can find an array of comfortable and conveniently located vacation rentals. This area offers a blend of lively community charm and easy access to local amenities, making it an ideal choice for your stay. Whether you're seeking a peaceful retreat or a lively atmosphere, Southside provides a diverse range of options that cater to every traveler’s needs. With its strategic location within Jacksonville, your vacation rental will serve as a perfect base to explore everything this dynamic city has to offer.
Downtown Jacksonville
In the heart of the region, this area offers easy access to business districts and cultural venues, making it an ideal spot for those seeking vibrant city life during their stay.
View 211+ Rentals in Downtown JacksonvilleBaymeadows
Known for its convenient location near major highways, the neighborhood provides a comfortable base for exploring the local region while enjoying suburban tranquility.
View 63+ Rentals in BaymeadowsIsle of Palms
Situated close to the coast, this community offers a peaceful environment with easy access to beaches, perfect for relaxing seaside getaways.
View 37+ Rentals in Isle of PalmsSan Marco
Famous for its charming architecture and boutique shopping, this neighborhood combines historic elegance with modern comforts in the local region.
View 131+ Rentals in San MarcoSouthpoint
Offering a blend of commercial development and residential areas, Southpoint is an excellent choice for travelers seeking convenience and accessibility.
View 29+ Rentals in SouthpointMandarin
Rich in natural beauty and local charm, this area provides a serene environment with proximity to parks and scenic waterways.
View 74+ Rentals in MandarinMiramar
This part of the region features quiet streets and lush greenery, ideal for visitors wanting a peaceful retreat within reach of city amenities.
View 587+ Rentals in MiramarDeerwood
Known for its upscale communities and golf courses, Deerwood offers a luxurious setting for those seeking an elegant stay in the local area.
View 45+ Rentals in DeerwoodBest Times to Visit Southside
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, allowing you to enjoy the area's pleasant climate and vibrant local events at their best.
Peak Season Highlights
Spring (March to May)
During spring, the region experiences pleasant weather, making it an ideal time to enjoy outdoor activities and explore the local scenery. This season attracts visitors looking for comfortable temperatures and a lively atmosphere.
Fall (September to November)
Fall offers cooler temperatures and vibrant seasonal colors, drawing travelers seeking a more relaxed experience. It's a popular period for those wanting to avoid peak summer crowds while still enjoying good weather.
Off-Season Highlights
Summer (June to August)
Summers can be hot and humid here, often leading many to prefer visiting during early mornings or late evenings. Lower occupancy rates provide a quieter stay for those seeking peace along with warmth.
Winter (December to February)
In winter, the region experiences milder temperatures, making it suitable for indoor activities and less crowded accommodations. It’s an excellent choice if you prefer a tranquil escape without the peak-season hustle.
Weekly Weather Forecast for Southside
How to Book Your Southside Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Southside
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax and cool off during your stay in the region.
- Take advantage of spacious outdoor patios or decks for dining and entertaining outdoors.
- Benefit from lush, landscaped gardens that enhance your outdoor living experience here.
- Utilize outdoor grilling facilities for convenient barbecues with friends or family.
- Make the most of nearby walking trails or bike paths to explore the scenic surroundings.
- Relax in outdoor lounge areas designed for soaking up the sunshine in this destination.
- Consider properties with secure, fenced yards ideal for pets or children to play freely.
Top Attractions Around Southside
What attractions are nearby?
During your stay, you can enjoy a variety of nearby activities, from exploring local parks to experiencing vibrant dining options in this area of Jacksonville, Florida.
Family Activities
- Jacksonville Zoo and Gardens: You can enjoy a day exploring diverse animal exhibits and beautifully maintained gardens perfect for family outings.
- Hands-on Children's Museum: This interactive museum offers engaging activities that inspire curiosity and creativity for children of all ages.
- Camp Milton Historic Preserve: Experience a blend of history and outdoor adventure as you explore historic sites and scenic trails suitable for family exploration.
- Sunset Pier Park: Relax with your loved ones by the water while enjoying picnics, playground fun, and scenic views in this popular local park.
Adult Activities
- Golfing at the St. Johns Golf & Country Club: Enjoy a day on the lush fairways of this renowned golf course, perfect for both amateurs and seasoned players seeking a relaxing outdoor activity.
- Shopping at The Avenues mall: Explore a variety of retail stores, restaurants, and entertainment options in one of the area's premier shopping destinations, ideal for leisure and social outings.
- Dining in local eateries: Savor diverse culinary delights at popular restaurants that showcase regional flavors, making it easy to indulge during your stay here.
- Visiting nearby parks and recreational areas: Unwind in scenic green spaces offering walking trails and outdoor activities, providing a refreshing escape in this vibrant part of the city.
Other Places to Stay in Southside, FL
Southside Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's diverse culinary scene to enjoy authentic flavors and unique eateries near your vacation rental in Southside.
- Visit Nearby Shopping and Entertainment Venues: Make the most of your stay by discovering shopping centers and entertainment options conveniently located around this destination.
- Plan Outdoor Activities: Engage in outdoor pursuits, such as parks or scenic spots in the region, to experience the natural beauty while staying close to your accommodation.
- Utilize Local Transportation: Use available transit options or rental services to easily navigate the area and access popular attractions in the neighborhood.
Transportation Options
- Jacksonville Transportation Authority (JTA) Bus System: You can conveniently rely on the local bus network to explore the area and reach major destinations near your vacation rental.
- Rental Car Services: Renting a car provides flexibility to discover more remote attractions and navigate comfortably around this vibrant region.
- Ride-Sharing Options: Popular services like Uber and Lyft offer quick and reliable transportation right from your vacation rental here in the area.
- Public Transit and Commuter Trains: The regional transit system allows easy access to different parts of Jacksonville, making travel hassle-free during your stay.
Local Customs Options
- Southern Hospitality: You can often expect warm welcomes and friendly interactions that reflect the region’s famed southern hospitality in your stay here.
- Local Seafood Cuisine: Sampling fresh seafood dishes is a cherished custom, offering an authentic taste of this destination’s coastal culinary traditions.
- Community Festivals: Participating in local festivals provides insight into the area's vibrant culture and helps you connect with residents sharing their traditions.
- Respect for Nature: Visitors typically observe a strong appreciation for preserving the region’s natural beauty through eco-friendly practices and outdoor etiquette.
Frequently Asked Questions About Southside?
1. What are the top vacation rentals in Southside?
There are a lot of options in Southside. If you plan on staying in the Southside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Southside:
- AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin
- Pet Friendly Studio with Tons of 5 Star Reviews
- Adorable Condo - 2 blocks from San Marco Square!
- Family-Friendly Beach Retreat With Pool By Mayo
- Beautiful Coastal Home near Mayo Clinic. Pet Friendly!
- 2 Full Beds | Suite, Non-Smoking, Kitchen
- 1 King Bed | Non-Smoking, Kitchen
- 1 Full Bed | ADA/Tub/Non-Smoking/Kitchen
- 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
- Enjoy this modern brand-new townhouse located in the heart of Jacksonville.
2. How many vacation rentals have private pools in Southside?
There are 69 vacation rentals with private pools near Southside. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Southside are best for families?
If you are looking for a family-friendly vacation home in Southside, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Southside:
4. How many Rentbyowner vacation rentals are available in Southside?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1317 in the Southside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Southside.
5. What is the cancellation policy for vacation rentals in this area?
6. Are there any additional fees I should be aware of when booking here?
7. How do I ensure my reservation is secure and confirmed?
8. What amenities are available at vacation rentals in this destination?
9. Is there a check-in or check-out time I should know about?
Southside Top Rated Vacation Rentals
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
10.0- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
10.0- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
10.0- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
