Southside holiday rentals

We found 517 holiday rentals — enter your dates for availability

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June 2025

July 2025

Select from 269 houses, 195 apartments and other holiday rentals to find the perfect place for your stay in Southside. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include parking and a garden. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Southside

Showing deals for:12 Sept - 19 Sept

Exceptional

(106 reviews)

Mayo Clinc 1mile from Intercoastal waterfront home w/pool and Breathtaking Views

Jacksonville Beach, FL

9% off

S$489 per night

includes taxes & fees

Pool, sitting area, enjoy the beutiful sunsets from lounge chairs

Exceptional

(18 reviews)

SUMMER SPOT! Luxe Poolside Escape_Grill_In Julington Creek~Sleeps 10

Jacksonville, FL

7% off

S$370 per night

includes taxes & fees

Exceptional

(15 reviews)

Manatee House: Private Marsh View Retreat - 1 Mile to Mayo, 5 Miles to Beaches

Jacksonville, FL

7% off

S$401 per night

includes taxes & fees

Exceptional

(23 reviews)

Big Wheelchair Accessible Home Close to Beach/Mayo with Zen Den and Fenced Yard

Jacksonville Beach, FL

11% off

S$336 per night

includes taxes & fees

Very good

(5 reviews)

Charming 3-beds 2- baths house with AC/heat+WiFi in Jacksonville FL. First cos

Jacksonville, FL

8% off

S$181 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Southside

Mayo Clinic Florida

Find the best place to stay - Southside

Showing deals for: 7 Sept - 10 Sept

Private pool in our spacious backyard, no neighbor in the back!

Heated Pool Oasis! 4bd/2ba, Arcades & Ping Pong!

Sleeps 10 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

S$422 per night

includes taxes & fees

Cush Jax Baymeadows Ranch, Close to Everything!

Sleeps 6 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

S$463 per night

includes taxes & fees

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Southside?

The most popular types of holiday rentals in Southside are apartments. Looking for something different? Vrbo has a variety of options to match the diverse needs of our guests, so you’ll see properties in loads of shapes and sizes. The perfect home away from home is waiting for you — find yours today.

How much does it cost to rent a holiday rental in Southside?

Length of stay, property type and time of year are some factors that can affect the price of a holiday home. Simply click on your travel dates to find your ideal escape. From quaint country cottages to expansive luxury villas, all Vrbo holiday rentals provide unbeatable value.

How much does it cost to rent a beach house in Southside?

Prices for beach houses in Southside may differ depending on the style and size of the property and time of year you’re travelling. Simply enter your dates of travel into Vrbo and the number of guests to view your options and prices. From there you can use the filters to narrow your search results by amenities, ratings, nearby activities and more.

Are there pet-friendly holiday rentals in Southside?

Yes. Pick from 375 holiday homes that roll out the welcome mat in Southside on Vrbo. Our cuddly best friends need to get away from it all too, so simply use our search function for pet-friendly holiday rentals to find a pad where your doggie can join in the fun.

Can I rent a house with a pool in Southside?

Tick the “pool” box in our handy filter tool and pick from 161 houses with private pools in Southside on Vrbo. Lazy soak or ball games and races? How you spend your leisure time is up to you when your Vrbo holiday property comes with a swimming pool.

What are popular rental amenities in Southside?

A garden, a chef and a nearby waterfront are rated the most popular rental amenities in Southside. Whether you plan to travel as a party of one, with your better half or a group of family members, Vrbo will help you find a holiday home that suits your tastes with all the features you’ll enjoy.

Are there large group holiday rentals in Southside?

You can choose from 19 holiday properties in Southside that can sleep 10 or more people. Whether you’re planning time away with extended family or a celebration like a birthday, there’s plenty of room to get your loved ones together under one roof.

Are there holiday rentals in Southside that welcome kids?

Southside has 375 family-friendly holiday rentals to pick from. And booking a stay that welcomes kids is super easy with our “Properties good for families” filter. In addition to having the whole place to yourselves, you can also look forward to conveniences and perks like living rooms, kitchens and yards.

What are the top attractions for families in Southside?

Keep the kids busy at these fantastic family-friendly attractions in Southside:

Mandarin Museum
Latitude 30
Hands on Childrens Museum

Are there one-bedroom holiday rentals in Southside?

Yes, you can take your pick from 117 one-bedroom rentals in Southside. Whether you’d prefer a cosy chalet or a cabin, Vrbo’s one-bedroom properties are perfect if you don’t require tons of space. One of the main perks of having your own digs? You’ll never need to share your trip with strangers.

Can I find two-bedroom holiday rentals in Southside?

Southside has 109 two-bedroom holiday properties for you to select from. Go for a holiday home with all the comfort and space you need at a price you’ll love on Vrbo.

Are there holiday rentals with WiFi in Southside?

You can pick from 178 holiday rentals with WiFi in Southside. If you’d like to disconnect from the world on your break, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find holiday rentals with air conditioning in Southside?

Southside has 369 holiday rentals where you’ll be able to wind down in air-conditioned comfort. To find a stay on Vrbo offering this amenity, enter your travel dates and use the convenient filters to select the “air conditioning” box.

How old do you have to be to rent a holiday rental in Southside?

The age limit can differ between properties on Vrbo, so double-check the rules of the holiday home in Southside you’re considering. But typically, it’s 16, 18 or 21.

How long can I rent a holiday rental in Southside for?

It really depends on the Southside property. To browse available options offering extended stays, just enter your dates and guest number into the Vrbo search page. You can look forward to having the whole place to yourself, along with comforts such as a fully-equipped kitchen and a backyard where the little ones can play. Be on the lookout for any long-term stays that offer weekly or monthly discounts.