Vacation rentals in Southside, Jacksonville

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Top-rated vacation rentals in Southside, Jacksonville

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Guest favorite

Home in San Marco

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!

Guest favorite

Guest suite in Southeast Jacksonville

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.

Guest favorite

Home in Southeast Jacksonville

Quiet townhouse Backyard. Pet friendly. I-95.

The place is located in the heart of Mandarin, close to all main location. It is ideal for group of 4 people.The place has 2 bedrooms 2 bathrooms and was recently updated.Enjoy the privacy of the Florida room and fenced-in backyard.There are 1 parking spot in the garage and 1 spot in the driveway in the front of the house.Neighborhood is the quite, family-friendly.The place locates 5 minutes away from Whole Foods, Publix, UPS, and FedEx.There are a lot of good restaurants within 15 minutes away.

Guest favorite

Rental unit in Jacksonville

White Rock Studio

Parking Limited to 1 vehicle. Studio apt. attached to house but privately separated. Centrally located in Jacksonville, only a five minute drive to the beaches, and not far from everything else. Unit has all you need for a week long stay or just one night. With Full Kitchen and laundry. Decorative Lighted patio available for all guests. Comfortable Queen sized bed easily sleeps 2, crib available on request for infants younger than 2. Hosts are friendly and answer communications immediately.

Guest favorite

Guesthouse in Southeast Jacksonville

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

Rental unit in Southeast Jacksonville

Top floor modern getaway w/resort amenities!

New build! Entire modern, luxurious, and spacious apartment. Stunning lake-front view with gorgeous sunsets. Large king bed and queen sleeper sofa provide a comfortable stay for 4. Whether your stay includes a day of shopping, a trip to golf, going to work, or to unwind at the beautiful Jacksonville beaches, you are never far from your destination. Less than 5 miles to the St. Johns Town Center, 7 miles to the nearest hospital, 11 miles to the beaches, and 6 miles to the nearest golf course.

Guest favorite

Guesthouse in Murray Hill

Large 1 bedroom Cottage with full kitchen

This is a full size one bedroom house with full brand new kitchen and private entrance. The entire place was renovated late 2021. A luxurious king size bed awaits you and a twin sized sofa bed for one adult or two kids. The kitchen has a full sized brand new oven, stove, microwave, dishwasher and fridge and is stocked with utensils etc so you can easily make full meals or stay for an extended time. There's one free off-street parking spot available and plentiful free street parking.

Guest favorite

Home in Jacksonville

Cozy Retreat By Mayo, Beach, Pet Friendly Backyard

Send me a message for SUMMER KICKOFF 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

Rental unit in Southeast Jacksonville

Jacksonville resort style getaway

"Welcome to our resort feel one-bedroom oasis. Relax by the sunny poolside, sip on drinks, and indulge in a resort style vibe. We're here to ensure your stay is unforgettable - from recommending the best local spots to providing personalized service. Book now for a remarkable vacation!" Please just book and do not ask for pre approval because it blocks my dates off and some of you don’t end up booking and I end up losing on other potential bookings . Thanks in advance

Guest favorite

Home in Southeast Jacksonville

Cozy Urban Home.

Comfortable and affordable home. It is a smoke free, pet free and cozy house. Located in a quiet neighborhood. Great place to rest . NO Pets , 0 tolerance for parties or Gatherings , smoke free home . 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 "

Guest favorite

Rental unit in Southeast Jacksonville

"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!

Guest favorite

Guesthouse in Riverside

Enchanted Forest: a Magical Luxury Studio

Lost to time, at the end of a long forgotten forest path, where dappled sunlight outline trees, moss, and stone. Enjoy the luxurious richness of satin, velvet, chandeliers and candles. Looking to escape, we’d love to share the path to this hidden destination in Historical Riverside. Equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.