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.

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Guest favorite

Home in Southeast Jacksonville

4.96 out of 5 average rating, 241 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

Superhost

Tiny home in Southeast Jacksonville

4.84 out of 5 average rating, 282 reviews

Private yard, all secluded tiny house-your oasis!

Come play at the beach! 24’ tiny house on a private fenced yard with gas grill, tropical outdoor area for relaxing. Lofted sleeping space, with shower and toilet make this the perfect weekend getaway or the escape from work meetings. Close to Mayo Clinic, Downtown , & Florida Beaches all a 15 minute drive! Or enjoy Orlando and natural springs with manatees couple hours away. St Johns town outdoor mall is a 5 minute drive and has countless food and shopping options! Truly a unique experience!

Guest favorite

Guesthouse in Southeast Jacksonville

4.91 out of 5 average rating, 229 reviews

Studio Suite in Beautiful Central Neighborhood

Studio guest suite with queen bed and kitchenette in beautiful Miramar neighborhood, just 5 minutes from historic San Marco. Close to restaurants, grocery, MD Anderson Cancer Center and Wolfson Children's Hospital. Owners live in main house on site but suite has its own private entrance and parking. You will have access to an outdoor dining space and fenced in backyard. Dogs live on premises but will not interfere, although you may hear barking. Sofa bed available if needed, please inquire.

Guest favorite

Home in Jacksonville

4.98 out of 5 average rating, 171 reviews

Cozy Retreat By Mayo, Beach, Pet Friendly Backyard

Send me a message for the WINTER WONDERLAND discount Local private host delivering exceptional 5 star experiences nestled in this quiet neighborhood Luxurious beds and blackout curtains offer a relaxing oasis to enjoy your stay. Gather around our large table with family and friends to make memories Pet & family friendly! Sleep 7 guests Convenient to Cruise Terminal, Beach, Mayo, and Shopping/ Dining Private fenced in backyard In Unit Washer/ Dryer DBPR DWE2613890 TDT #1871 LBT #412575

Guest favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 363 reviews

Private Apartment

Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen. Property access for our guests only. Complimentary beer, sodas, water and coffee! Adults only.

Guest favorite

Home in Southeast Jacksonville

4.84 out of 5 average rating, 189 reviews

Private FL Home with Pool, Hot tub & Luxury Master

This is a lovely family home in the Mandarin area of Jacksonville which has undergone many renovations and upgrades. The master boasts its own, ensuite, tv, fireplace and sitting area, as well as a private entrance from the pool and hot tub area. The house itself has newer furnishings, flooring, modern decor, a large fenced in backyard, pickle ball court and firepit. Located safe South East Suburb of Jacksonville, not far from shopping, beaches and many other Florida attractions.

Guest favorite

Home in Avondale

4.99 out of 5 average rating, 99 reviews

Fancy Dancy

Experience the charm at "Fancy Dancy". Nestled within Avondale’s historic community, this home is strategically located within walking distance to a plethora of restaurants, parks, boutiques, and the serene St. Johns River. For the Sports fans, Jacksonville Jaguars stadium is only a 10 min drive. Whether you're seeking culinary delights, outdoor adventures, or sporting events, everything you desire is just steps away. Discover the perfect blend of comfort, style, and convenience.

Guest favorite

Guesthouse in Southeast Jacksonville

4.96 out of 5 average rating, 171 reviews

Il Rifugio waterfront retreat on the ICW by Mayo!

This peaceful, quiet location on the intercoastal waterway is a perfect place to get away or stay close to Mayo clinic and relax among the bald eagles, owls, dolphins, manatees, etc. Completely private building with raised patio area for you to enjoy. Sleeps up to 4 (1 king size + 1 full size beds) . Close to beaches (4 miles), restaurants, Mayo clinic, 2.5 miles; TPC/ Sawgrass Golf ,10 miles; Saint JohnsTown Center shopping 10 miles; Jacksonville International Airport, 25 min.

Guest favorite

Home in Southeast Jacksonville

4.94 out of 5 average rating, 147 reviews

Cozy Urban Home.

Comfortable and affordable home. NO Pets , 0 tolerance for parties or Gatherings , smoke free home . Located in a quiet neighborhood. Great place to rest . No exceptions about parties or hosting any type of gatherings at this property Location : This is a good choice if you are here for a concert, game , visiting Jax or simply need palace to rest. Accessibility: House layout features steps on all points of entry , and a small bathroom. Please see "Other Details to Note "

Superhost

Bungalow in Southeast Jacksonville

4.8 out of 5 average rating, 258 reviews

San Marco Area Bungalow * Cozy Screened Porch*

Welcome to Stylish Historic San Marco charming bungalow with cozy front porch, the perfect retreat for your next Airbnb getaway! Nestled in a peaceful neighborhood, this adorable bungalow offers a cozy and inviting atmosphere that will make you feel right at home. Centrally located making it convenient to downtown, medical facilities, beaches and more. *There are other cottages next door, perfect for groups or families that want to stay in the same location.

Guest favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 269 reviews

Blue Bird Paradise

Welcome to “Bluebird Paradise”. Come visit our bright, beautiful, 400 sq. ft “Guest House”, detached from our home with a porch overlooking our beautiful Florida backyard with pool. The commute is very good; it is located less than 30 minutes from the city, 30 minutes from the beach and 30 minutes from the famous historical St Augustine. Peace and quiet await you. A guesthouse is a detached building that shares the property with the host.

Guest favorite

Rental unit in Southeast Jacksonville

5 out of 5 average rating, 213 reviews

"Sweet Water" Waterfront Studio Apartment

Experience inter-coastal living in a well-appointed waterfront, upstairs studio guest house. Furnished with a queen bed, full-size sleeper sofa & many amenities. Only minutes from the beaches, Mayo Clinic, restaurants, nightlife, Players Championship Golf Course, shopping & more. Conveniently located near lots of activities, but not too close to interfere with your rest & relaxation. Whether on vacation or business, it's the ideal location!