Vacation rentals in Southside, Jacksonville

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Top-rated vacation rentals in Southside, Jacksonville

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Southeast Jacksonville

4.98 out of 5 average rating, 158 reviews

Coastal Lane 3/2 Clean Home in Jacksonville, Wi-fi

Reach out about our multi day discounts for weekdays! This gorgeous 3 bedroom coastal style home is your home away from home! Located in a peaceful and quiet neighborhood with perfect lake views. It's close to shopping, stores, and restaurants. - Easy highway access right off I-95 - 15 minute drive from the Jacksonville Jaguars Stadium (TIAA Bank Field) - 20 minute drive to Jacksonville Beach - 25 minute drive to Jacksonville Airport - Fast Wi-Fi -EV Charge Available for Guests in Garage

Nov 16 – 23

ﺩ.ﺇ681 per night
Guest favorite

Guest suite in Southeast Jacksonville

4.89 out of 5 average rating, 103 reviews

Cute private guest suite in charming neighborhood

Whether you are visiting for work, vacation or planning a local getaway, our guest suite is thoughtfully set up to provide what you need for your stay. In a friendly, residential area we are located on quiet street, where large trees and greenery create a natural canopy, providing for a cool and cozy side yard for you to enjoy during your stay. Centrally located to many of Jacksonvilles popular attractions so you can enjoy peace and quiet while restaurants and shops are within walking distance.

Sep 14 – 21

ﺩ.ﺇ275 per night
Guest favorite

Home in San Marco

4.98 out of 5 average rating, 209 reviews

Luxurious Craftsman in Historic San Marco

Never Drive Again! Immaculately renovated San Marco Bungalow, just a minute from excellent restaurants, retail, entertainment, hospitals & easy transit (via San Marco's FREE Beachside Buggy App) to everything else. Features include an inviting front porch, interior foyer, charming living room w/gas fireplace, new kitchen w/SS and granite, indoor laundry, historic architectural features, and private backyard w/ sitting area, fire pit, games & BBQ! Incredible location with unmatched walkability!

Aug 25 – Sep 1

ﺩ.ﺇ608 per night

Popular amenities for Southside, Jacksonville vacation rentals

Stay near Southside, Jacksonville's top sights

St Johns Town Center418 locals recommend
Topgolf134 locals recommend
The Avenues54 locals recommend
Memorial Hospital6 locals recommend
Mayo Clinic57 locals recommend
Alhambra Theatre & Dining37 locals recommend

Other great vacation rentals in Southside, Jacksonville

Guest favorite

Guesthouse in Jacksonville

4.94 out of 5 average rating, 31 reviews

La Casita on Jupiter

Jul 6 – 13

ﺩ.ﺇ235 per night
Guest favorite

Apartment in Southeast Jacksonville

4.87 out of 5 average rating, 23 reviews

Jacksonville resort style getaway

Jun 2 – 9

ﺩ.ﺇ358 per night
Guest favorite

Guesthouse in Jacksonville

4.97 out of 5 average rating, 30 reviews

Luxury Cottage with River Access

Jun 20 – 27

ﺩ.ﺇ441 per night
Guest favorite

Townhouse in Southeast Jacksonville

4.94 out of 5 average rating, 48 reviews

Cheerful 2 bedroom townhome with indoor fire place

Jan 23 – 30

ﺩ.ﺇ431 per night
Guest favorite

Apartment in Southeast Jacksonville

4.93 out of 5 average rating, 27 reviews

Boho Style 1 Bedroom King Bed Central Location

Jun 20 – 27

ﺩ.ﺇ524 per night
Guest favorite

Guesthouse in Mandarin

4.97 out of 5 average rating, 74 reviews

Charming, Pet Friendly Retreat in Heart of NE FL

Apr 5 – 12

ﺩ.ﺇ433 per night
Guest favorite

Home in Jacksonville

4.99 out of 5 average rating, 90 reviews

Cozy Retreat By Mayo, Beach, Pet Friendly Backyard

Aug 25 – Sep 1

ﺩ.ﺇ434 per night
Superhost

Apartment in Southeast Jacksonville

5.0 out of 5 average rating, 4 reviews

Lux Haven Stylish Jax Southside Beach Mayo Clinic

Jan 29 – Feb 5

ﺩ.ﺇ553 per night
Guest favorite

Apartment in Southeast Jacksonville

5.0 out of 5 average rating, 24 reviews

Grand Retreat w/Pool, Gym, Tennis Court, King Bed

Aug 1 – 8

ﺩ.ﺇ531 per night
Guest favorite

Guest suite in Southeast Jacksonville

4.98 out of 5 average rating, 46 reviews

The Petite Retreat- Walk to Mayo Clinic!

May 10 – 17

ﺩ.ﺇ378 per night
Guest favorite

Apartment in Southeast Jacksonville

4.8 out of 5 average rating, 76 reviews

Pet Friendly Retreat |2Bed-2Bath | 10/10 Location

May 22 – 29

ﺩ.ﺇ558 per night
Guest favorite

Apartment in Jacksonville

4.98 out of 5 average rating, 42 reviews

Peaceful Lakeview Ste Nr NAS, Hosp, & Mall

May 8 – 15

ﺩ.ﺇ414 per night

Quick stats about vacation rentals in Southside, Jacksonville

Total rentals

1.4K properties

Rentals with dedicated workspaces

820 properties have a dedicated workspace

Rentals with a pool

590 properties have a pool

Pet-friendly rentals

510 properties allow pets

Family-friendly rentals

740 properties are a good fit for families

Total number of reviews

35K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Duval County
  5. Jacksonville
  6. Southside