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 stars2 weeks 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

A tranquil villa is reflected in the calm surface of a pond, surrounded by lush greenery and trees. The two-story structure features a welcoming front porch with seating, and a backdrop of trees adds to the serene landscape.

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 stars2 weeks 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 stars3 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!

Guest favorite

A wooden pier extends over calm blue waters, inviting visitors to stroll along its length. People can be seen enjoying the ocean view, while a small beach umbrella provides shade. The clear sky above complements the serene coastal scene.

Condo in Beaches

4.82 out of 5 average rating, 110 reviews

Fun in the Sun - OCEAN FRONT!

WandaRating, 5 stars6 days ago

Prefect Place! ❤️ We enjoyed everything about our stay! The location was excellent … not far from Mayo for our doctor’s appointments. We could sit on the couch and watch the ocean or walk the short, quiet, private trail to the beach. It was easy to access with clear instructions. It was very clean and had everything one would need. It was a joy to stay here and I would definitely LOVE to stay again! I highly recommend it😊

Guest favorite

Home in Beaches

4.94 out of 5 average rating, 251 reviews

2 Kings + 2 bunks, Walk to Beach - $0 Host fee

JenRating, 5 stars1 week ago

We picked the house because of the proximity to the beach and kid-friendly aspects (beach toys, pack n play, etc) and we were not disappointed! We did walk to the beach (no parking by the access on 37th St), which was manageable with the wagon we brought from home and the beach cart at the house. My kids (5 & 2.5) enjoyed playing with the toys at the house and beach toys. The kitchen is also fully stocked and Ben was easy to communicate with. We have family in the area and expect that we'll be back again in the future!

Superhost

A private balcony is showcased with outdoor seating, offering a round table and two comfortable chairs. The oceanfront view reveals the sandy beach and clear blue sky, creating a serene seaside atmosphere.

Condo in Fernandina Beach

4.75 out of 5 average rating, 4 reviews

Sunrise Shores~insane view

JulieRating, 5 stars3 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.

Vacation rentals for every style

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Apartments

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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

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

The kitchen features a modern design with white cabinetry and a mosaic tile backsplash. Black appliances, including a microwave and coffee maker, are visible. A stainless steel countertop reflects light, while a window allows natural light to illuminate the space.

Home in Beaches

4.97 out of 5 average rating, 186 reviews

Casa Ramona - At The Beach!

AysegulRating, 5 stars6 days ago

We had a wonderful stay with kids. I could do my my jogging and sports in the morning at the park where is very close to the house. Very comfortable bedrooms, each with their osn bathrooms. Everything is thought for the comfort and joy. Beach umbrellas, chairs were ready, and even toys for the kids. I definitely recommend the location as well.

Guest favorite

The open kitchen and dining area features contemporary cabinetry, stainless-steel appliances, and quartz countertops. A round dining table with four chairs is set near a large window, while a spacious island with bar seating is available for casual dining.

Home in Fernandina Beach

5 out of 5 average rating, 14 reviews

Casa Azul

EmilyRating, 5 stars1 week ago

Gorgeous first-floor of a house just steps from American Beach! Very modern and updated. Beautiful kitchen and communal space. Great for a group!

Top guest favorite

Townhouse in Beaches

4.97 out of 5 average rating, 114 reviews

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

TracyRating, 5 stars4 days ago

This place was exactly as described and very clean. There were a lot of extras for the beach and a wagon to pull to them in. It exceeded our expectations. The three full bathrooms in each room is a plus. The kitchen had everything we needed. Elizabeth was a great communicator and took great care to ensure our stay was perfect. We would definitely stay here again!

Guest favorite

A serene outdoor space features a well-maintained lawn leading to a peaceful lake view. A stone pathway meanders through the grass, while natural greenery and shrubs surround the area. The distant water reflects the clear blue sky, enhancing the tranquil ambiance.

Home in Jacksonville

5 out of 5 average rating, 21 reviews

Waterfront paradise

CorinthiansRating, 5 stars1 week ago

It was just what we needed. Very accommodating , it was what had been described. Huge rooms . It was great would use it again

Superhost

Home in Ponte Vedra Beach

4.84 out of 5 average rating, 73 reviews

Beachfront Paradise Ponte Vedra

TeddyRating, 5 stars1 week ago

We had a terrific week staying as a family in this place. 6 adults and an infant, everybody had plenty of space and privacy but was also able to comfortably hangout in the living areas. The beach is amazing and the large table and grill in the backyard were perfect for enjoying family meals. We really appreciated how responsive you were to our needs. Great communication when we had a little trouble with the Airbnb App itself, and the early check-in and late check-out ended up being handled easily. Thanks again!

Guest favorite