Vacation rentals in Southside, Jacksonville

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Top-rated vacation rentals in Southside, Jacksonville

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

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Guest favorite

A modern living room features light grey leather sofas with built-in charging stations. A rectangular coffee table is placed on a textured blue area rug, while a floor lamp provides illumination. A doorway leads to a separate area, adding depth to the space.

Home in Southwest Jacksonville

4.92 out of 5 average rating, 25 reviews

Tasteful 3/2 vacation rental

ShantellRating, 5 stars2 months ago

I had a wonderful experience! Carleshia was responsive and attentive throughout my stay, providing exceptional customer service. Her care and attention to detail made my visit comfortable and enjoyable. I highly recommend staying here and would definitely book again!

Guest favorite

Townhouse in St. Augustine

4.91 out of 5 average rating, 129 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

Ann MarieRating, 5 stars1 week ago

A slice of heaven for the week. We would definitely return to Inga's beautiful beach house. We already recommended it to our family and friends! The location is great. Quiet community and within minutes to beach, and about 10 mins. to the Publix grocery store. The St. Augustine historic center is about 20 minutes away. Inga is quick to respond and adequately communicated. The home is spotless and well appointed with all you need for a comfortable and memorable reprieve. Thank you!

Guest favorite

Home in St. Augustine

4.89 out of 5 average rating, 112 reviews

"The Coastal House" Water Views and a Golf cart!

Lindsay Rating, 5 stars2 weeks ago

We are so grateful to Tim and Melody for providing a space where our family could be at home for a long weekend. My partner and I are in the process of creating a blended family, so this time together - and the need for it to be peaceful and joyful - was especially important for our young kids. It was everything we could have hoped for and more. We will be back!

Guest favorite

Villa in Jacksonville

4.88 out of 5 average rating, 101 reviews

Country villa pool hot tub game rm pond 2.5 acres

JenniferRating, 5 stars1 week ago

Curtis was very helpful and accomodating! I held a women's art retreat at the property. The ladies loved the beauty and the peaceful property. The home had everything we needed. We were sad to leave. I would definitely go back of its available! Thanks for a great weekend!

Guest favorite

A spacious outdoor patio area features a ceiling with wooden beams and overhead fans. Two hanging chairs provide seating, while a stylish seating arrangement is visible. A heated pool is situated in the background, complemented by a manicured turf area and a shaded umbrella.

Home in Beaches

5 out of 5 average rating, 6 reviews

Family Beach Getaway w/ Pool & Sports Playground

AlisaRating, 5 stars2 weeks ago

This property was perfect for our family and friends spring break trip. The backyard is amazing and kept the kids entertained for hours. The house was well equipped and the beds were comfortable. The walk to the beach is about 10 minutes and the property has tons of really nice beach chairs and a wagon. The property is also minutes away from tons of restaurants and things to do. I only had one high maintenance request (squeaky doors waking my toddler up) while we were there and they had someone out within an hour to help which I appreciated so much. We would definitely stay here again!

Superhost

A spacious coastal residence is situated along the beachfront, featuring a bright blue roof and light grey siding. Palm trees and meticulously landscaped greenery frame the entrance, with a large patio area leading to the ocean views in the background.

Home in Ponte Vedra Beach

4.92 out of 5 average rating, 61 reviews

Beachfront Bliss w/Swim Jacuzzi l Victoria Shores

AshleyRating, 5 stars1 month ago

We are so grateful for Randy! This was an amazing location. Everything we needed to make our stay enjoyable was already there waiting for us. I would 100% recommend staying here. My kids had the best time and loved all of the beach toys that were neatly waiting for them. I can’t even tell you my favorite part. Everything was perfect.

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What guests are saying

Cane Cottage Oceanfront Oasis

4.97 out of 5 average rating, 93 reviews2 weeks ago

We absolutely loved our stay at the Cane Cottage — it was exactly what we were hoping for and then some. Cozy, comfortable, and perfectly set up for a relaxing family getaway. It felt like every detail had been thought of — from the well-stocked kitchen to all the little touches that made it feel like home. The location couldn’t be better — literally steps to the beach, which most days felt like our own private spot. Waking up to the sunrise every morning was such a treat, and we spent our days either posted up with a book, wandering down the beach, searching for shells, or heading into town to explore St. Augustine. It was the perfect mix of peaceful and convenient — easy to unplug and relax, but close enough to everything we wanted to do. Our family felt so at home here, and we’re already talking about when we can come back.

Cottage in Ponte Vedra Beach

What guests are saying

Sunrise Shores~insane view

5 out of 5 average rating, 3 reviews3 weeks ago

Gorgeous condo with breathtaking views! Accommodations spacious, well equipped, beautiful, comfortable, and luxurious. We biked to restaurants, pickleball, putt putt, and around the island. Enjoyed the restaurants suggested by Michelle as well as use of the outdoor grills. Lovely pool and beach.

Condo in Fernandina Beach

What guests are saying

Seaside Oasis:Waterfront View+Private Beach Access

5 out of 5 average rating, 8 reviews3 months ago

We asked a flood of clarifying questions and Morgan was so gracious and responsive throughout the entire process. When we mentioned one minor thing needing repair as fyi, she offered to send someone right away or around our schedule and she did. There was a welcome basket with items for s'mores and more! Most of the all, the house was absolutely impeccable and my friends tease me for wanting to re-clean upon arrival to most vacation destinations. Short drive to beach entrance, less than 5 minutes to Caps on the Water & Publix, and less than 10 minutes to downtown St. Augustine. The best of all the worlds! We definitely hit the AirBnB Jackpot this time! <3

Home in St. Augustine

What guests are saying

Walk 2 Beach | Game Room | Firepit |Heat/Salt Pool

5 out of 5 average rating, 93 reviews2 weeks ago

The house was beautiful and exactly what we needed! The neighborhood felt safe and quaint. We enjoyed walking to the beach and playing in the pool! The pool loungers were great for reading and napping! The house was a short drive to historic St Augustine. Jeremy and Laura were very responsive with any questions we had. We had a great experience and will book with them on our next trip!

Home in St. Augustine

What guests are saying

Beautiful Beachside Vacation Home W/ Amenities

4.9 out of 5 average rating, 90 reviews3 weeks ago

Christopher was such an amazing host! The home is even more beautiful than the pictures and truly GORGEOUS! A very short walk to the beach and the pool area was private and serene. The bed was sooooo comfy and everything was immaculate! Truly a gorgeous home, if you ever decide to sell, let me know Christopher LOL 10/10 recommend

Vacation home in St. Augustine

What guests are saying

Stylish 4 BR Beach Retreat - Steps to the Ocean~

4.98 out of 5 average rating, 40 reviews1 month ago

Haley and Trent have created a lovely atmosphere in their home. From the well-appointed furnishings and decor with a fully stocked kitchen to the multiple seating areas which allowed space to spread out, everyone in our party of 7 was happy to spend the week just a few minutes walk from the beach. The beach itself is uncrowded and pet friendly. Having beach towels and chairs as well as shower products available was great too. The beds were very comfortable. Access to a grocery is only a few miles down the road. Getting into the heart of St. Augustine from the house takes only minutes. Both were very responsive to communication before and during the rental period. We are seasoned travelers, and this house was one of the few that actually lived up to its photos and description.

Home in St. Augustine

What guests are saying

Island Breeze in Vilano Beach-5 min walk to beach

4.9 out of 5 average rating, 88 reviews2 weeks ago

We had a fantastic family stay at Elizabeth’s place in Florida! The house was spotlessly clean, beautifully maintained, and had absolutely everything we needed for a comfortable and relaxing stay. The kitchen was very well-equipped, which made cooking meals a breeze. We especially appreciated the bicycles and beach gear provided—it made our trips to the beach so easy and fun. The location is perfect—just a 5-minute walk to the beach, where we enjoyed stunning sunrises every morning. It’s also a short drive to St. Augustine’s city centre, which made exploring the area super convenient. Despite being so close to everything, the neighbourhood was peaceful and quiet, perfect for unwinding after a day out. Elizabeth was a fantastic host—very communicative, thoughtful, and accommodating throughout our stay. We felt well taken care of from start to finish. We’ve already recommended this place to friends and family, and we’d definitely stay here again on our next trip to the area.

Townhouse in St. Augustine

What guests are saying

Cozy Coastal Beach Home - Hot Tub! Pets! Bicycles!

5 out of 5 average rating, 22 reviews4 weeks ago

What a great house. The description was exact. The house is in a cul-de-sac sorry it was a quiet street. The beach was a 5 minute walk and a water front restaurant just a 2 minute walk. Holly answered all of our questions, including my son’s Xbox question we didn’t know he was asking. She was great with it all. The bikes and all the beach supplies worked out perfect for us. The home was spotless and the hot tub was a hit. Thanks again holly and we will be back again.

Cottage in St. Augustine

What guests are saying

Vilano's Very Best

5 out of 5 average rating, 13 reviews6 months ago

JT was an awesome and thoughtful host. The property was modern and well equipped. Loved the location and everything about it. When the hurricane came in JT was responsive, compassionate and worked tirelessly with the power company to get power restored. Couldn’t have asked for a better host and property for our stay!

Home in St. Augustine

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Popular amenities for Southside, Jacksonville vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Southside, Jacksonville's top sights

EverBank Stadium134 locals recommend

Riverside Arts Market173 locals recommend

Topgolf134 locals recommend

TacoLu140 locals recommend

Five Points138 locals recommend

Hawkers Asian Street Fare137 locals recommend

Other great vacation rentals in Southside, Jacksonville

Top guest favorite

Home in Ponte Vedra Beach

5 out of 5 average rating, 23 reviews

TPC Sawgrass Coastal Getaway

JaniceRating, 5 stars3 months ago

Lucus was very responsive and accommodating. His home was well stocked with everything you might need. Coffee bar, snacks, and drinks were available. The bath towels were thick and fluffy. ( I loved the shampoo but forgot to write down the brand.) The location is very secure and we felt very safe in his lovely neighborhood. The place did not feel like a rental but more like we were visiting friends.

Guest favorite

Apartment in Southeast Jacksonville

4.91 out of 5 average rating, 23 reviews

Lux King Bed Balcony Pool View Southside St Johns

EvelynRating, 5 stars2 months ago

My stay at this apartment was wonderful—it truly felt like home! The space was clean, quiet, and comfortable, making it the perfect place to relax. I would definitely stay here again. Highly recommend!

Top guest favorite

A spacious bedroom features a light wood floor and a large white bed adorned with blue and white pillows. A cozy accent chair sits beside a dresser, while sliding glass doors provide access to a balcony, allowing natural light to fill the room.

Townhouse in Beaches

4.97 out of 5 average rating, 112 reviews

200 ft to toes in the sand! Restaurants! Shopping!

PamRating, 5 stars1 week ago

Amazing return visit! This was our second time at Elizabeth’s place and it was fantastic. The townhome was spotless and Elizabeth is easy to get ahold of if anything is needed. The location is perfect- walkable to beach, shops and restaurants. Kitchen is updated and well appointed. Thanks for a lovely stay!

Guest favorite

A bright living area features a large television mounted on a wall above a sleek entertainment unit. Comfortable seating is provided by fabric chairs and a large tufted ottoman, while a green plant adds a touch of nature to the space.

Home in Jacksonville

4.89 out of 5 average rating, 57 reviews

Lovely and spacious Florida get away

Shin-HaeRating, 5 stars1 month ago

Felicidad was very responsive to any questions or issues that arose. And home looked exactly like it did in the photos

Top guest favorite

A Spanish-style home is set amidst lush greenery, with a welcoming entrance illuminated by warm lights. A circular driveway curves gracefully towards the front door, while a picturesque sunset casts a beautiful glow over the property.

Villa in Southwest Jacksonville

5 out of 5 average rating, 9 reviews

Private Retreat at Romantic Spanish-Style Villa

NickRating, 5 stars3 weeks ago

Fantastic stay! The place was clean, stylish, and exactly as listed. The host was responsive and check-in was super easy. Quiet, safe neighborhood—would definitely stay again!

Guest favorite

A spacious primary bedroom features a king-size bed with a light blanket, complemented by a large window with natural light. Nightstands with lamps sit on either side of the bed. A closet and a doorway to an adjoining bathroom are visible, enhancing the room's functionality.

Home in Ponte Vedra Beach

4.92 out of 5 average rating, 59 reviews

Ponte Vedra Beach Coastal Getaway: Sleeps 8

EmilyRating, 5 stars1 month ago

Coco‘s place was great for what we needed. She accommodated last minute and it was located in a nice suburban neighborhood near the main highway. easy to get to the beach, restaurants, grocery store, shops, etc..

Superhost

A panoramic view of the ocean is framed by large windows, capturing the vibrant colors of a sunset. Soft orange and pink hues blend into the sky as waves gently lap at the shore. A lantern rests on the floor, adding a subtle touch to the serene setting.

Cottage in St. Augustine

4.71 out of 5 average rating, 21 reviews

Beachfront cottage, 5 minutes to Downtown

ClayRating, 5 stars2 months ago

The location and especially the proximity to the water compared to the neighbors is darn hard to beat. You can hear the waves crashing from most rooms when the door to the front porch is open. We had a great time and totally enjoyed our stay. My only critique is that most of the windows are painted shut or are inoperable for other reasons and the 2 bedrooms on the west/street side of the house get a fair amount of road noise. Regardless, this beach house is a winner.

Guest favorite

An outdoor area features a sparkling pool surrounded by a textured stone patio. Four wooden lounge chairs are arranged around a central table, enhancing the inviting space. Lush greenery and flowering plants provide a serene backdrop, while a covered area offers shade.

Home in St. Augustine

4.95 out of 5 average rating, 98 reviews

new 4 bedroom home, 2 master-suites and pool

EamonRating, 5 stars1 month ago

Great spot for our group spring break trip! House was prepared with everything we needed for our stay and we loved the pool. Short walk to a peaceful beach and easy drive to downtown St Augustine and nice restaurants. Would definitely recommend

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Quick stats about vacation rentals in Southside, Jacksonville

Total rentals
1.3K properties
Total number of reviews
39K reviews
Family-friendly rentals
710 properties are a good fit for families
Pet-friendly rentals
550 properties allow pets
Rentals with a pool
450 properties have a pool
Rentals with dedicated workspaces
810 properties have a dedicated workspace

Vacation rentals in Southside, Jacksonville

Top-rated vacation rentals in Southside, Jacksonville

Cane Cottage Oceanfront Oasis

Sunrise Shores~insane view

Seaside Oasis:Waterfront View+Private Beach Access

Houseboat - Boatiful Life

Walk 2 Beach | Game Room | Firepit |Heat/Salt Pool

Updated Home | Stadium | Beaches | Downtown | Zoo

Beautiful Beachside Vacation Home W/ Amenities

Stylish 4 BR Beach Retreat - Steps to the Ocean~

River Front hideaway, heated pool, amazing views.

Island Breeze in Vilano Beach-5 min walk to beach

Cozy Coastal Beach Home - Hot Tub! Pets! Bicycles!

Vilano's Very Best

Vacation rentals for every style

Popular amenities for Southside, Jacksonville vacation rentals

Stay near Southside, Jacksonville's top sights

Other great vacation rentals in Southside, Jacksonville

Quick stats about vacation rentals in Southside, Jacksonville

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Destinations to explore