Holiday rentals with breakfast in Southside, Jacksonville

Find and book unique Holiday Accommodation with Breakfast on Airbnb

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Popular amenities for Southside, Jacksonville Holiday Accommodation with Breakfast

Holiday House Rentals with breakfast

Guest favourite
Home in Murray Hill
4.88 out of 5 average rating, 72 reviews

Colorful Bungalow Sleeps 6 - Pet Friendly!

VictoriaRating, 5 stars1 week ago
thank you to Heidi for her colorful bungalow. we were there for our son's wedding, and we brought our first grandchild back to the bungalow to spend the night for their wedding present we felt right at home. we would definitely use this colorful bungalow again.
Top Guest favourite
Home in St. Augustine
4.97 out of 5 average rating, 68 reviews

Coastal St. Augustine Retreat, Quiet Neighborhood

ShawnaRating, 5 stars2 weeks ago
This was an ideal location to spend the night on our way to Orlando. The home is very easy to get to, was very clean and spacious, and was very close to stores and restaurants. Everything was just as pictured, looked to be brand new, and we would definitely stay again! Thank you.
Guest favourite
Home in Green Cove Springs
4.89 out of 5 average rating, 18 reviews

NEW 4BR home in Golf Community with POOL

KelliRating, 5 stars3 weeks ago
Was a great place to stay. We had a very minor issue with the AC when we first arrived. The host responded right away and let us know how to fix the issue. The house was just as described. We would definitely stay again.
Top Guest favourite
Home in St. Augustine
5 out of 5 average rating, 56 reviews

Pars•Sun•Fun | Golf Sim•Hot Tub•4min Walk To Beach

JulieRating, 5 stars2 weeks ago
5 Stars – A Perfect Stay! This was one of the best Airbnb experiences we’ve had. The home was exactly as described—clean, comfortable, beautifully styled, and thoughtfully equipped with everything we needed for a relaxing stay. The location was perfect, close to restaurants, Publix and a 3 min walk to the beach, yet peaceful and private. Our host (Seth) was incredibly responsive and kind, making check-in seamless and providing great local recommendations. We especially appreciated the bikes, beach equipment, toys, games, kitchen supplies and snacks! We would absolutely stay here again and highly recommend it to anyone looking for a top-tier Airbnb experience. Thank you for such a wonderful stay!
Guest favourite
Home in Ponte Vedra Beach
5 out of 5 average rating, 39 reviews

Direct Beachfront Private House 11 steps to beach

OferRating, 5 stars3 weeks ago
We had an absolutely wonderful stay at Amy and Matthew’s place. The beach is quiet, clean and gorgeous. Amy was extremely hospitable and checked in to make sure our stay was going well. The house is fully equiped and the beds were super comfortable! The location is also close to great grocery stores, restaurants and other amenities. We will be staying again for sure!
Guest favourite
Home in Jacksonville
4.8 out of 5 average rating, 94 reviews

The entire Wonderwood beach house! 3br / Hot Tub.

DanRating, 5 stars10 months ago
This was a wonderful house to stay at on our trip. The amenities were wonderful and the host was so accommodating. We would definitely recommend staying here and will be back!
Guest favourite
Home in St. Augustine
4.98 out of 5 average rating, 49 reviews

Twin Oaks Family Retreat, Sleeps 8, N St Augustine

KathiRating, 5 stars15 months ago
Karin was fast to respond and friendly. Her husband greeted us to let us in the house. While he was there, he gave us a tour of the home and told us where everything was located. We rode motorcycles in so space was limited on packing. The house had everything plus more than was needed. If we ever take another trip to Florida, we will stay here again.
Superhost
Home in St. Augustine
4.68 out of 5 average rating, 34 reviews

Cozy Beach House Of Your Dreams

SarahRating, 5 stars2 months ago
I love the charm of this home, chefs kitchen, the house felt spacious, we loved hanging out in the backyard and the front porch, close walk into town but close to the beaches too and lots of local restaurants in walking distance

Apartment rentals with breakfast

Apartment in St. Augustine
4.79 out of 5 average rating, 19 reviews

Historic Downtown St. Augustine Suite w/ Balcony,

RobertRating, 5 stars1 week ago
We use Airbnb all the time, this property ranks right up there with the best! It was bigger and newer than we expected. Super clean and very comfortable. Of course, the highlight is sitting on the balcony sipping wine and watching the continuous parade of humanity walk by. Everything you want is a short walk outside your door. We will be recommending this place to our family and friends!
Guest favourite
Apartment in Springfield
4.96 out of 5 average rating, 290 reviews

Historic Rustic Glam Abode

LizaRating, 5 stars1 month ago
The place was exactly as the pictures. Bed was nice and comfy and the kitchen and bathroom were clean. The home was furnished beautifully. We would book again.
Superhost
Private room in St. Augustine
4.82 out of 5 average rating, 11 reviews

Downtown Apartment in the Middle of it All

CapitolaRating, 5 stars10 months ago
I had the most amazing experience I had stayed here for a couple days and it was just better than I could have ever imagined. I was truly thankful to have that experience looking out over the bay it was just beyond beautiful perfect everything I needed was all nearby I couldn't ask for anything better. I will always come here when I come back to St Augustine. There are no words that can describe how amazing the experience was when I went there. 🙏❤️😇
Apartment in San Marco
4.93 out of 5 average rating, 15 reviews

Oasis in Historic San Marco

JonathonRating, 5 stars28 months ago
David was an excellent host. He was responsive and helpful throughout our visit
Top Guest favourite
Apartment in Riverside
5 out of 5 average rating, 24 reviews

Historic Jacksonville Utopia

KimberlyRating, 5 stars11 months ago
I loved the place and so did my family (boyfriend and 2 little children). I did tried to keep my son (5year old) from doing loud noises or stumping his autistic and has ADHD I thought I am glad this location was very patient with us thank you for everything would love to come back
Guest favourite
Apartment in Springfield
4.95 out of 5 average rating, 271 reviews

Fancy's Historic Apartment

BrendaRating, 5 stars2 days ago
This was a great peaceful place! Perfect for my work trip! I was literally close to everything great food near bye . The beach was only 30 minutes! Me and my daughther did a splash and paint room that wasn’t far it was amazing on fridays Jax beach has silent party on the pier for all ages but it was cancelled. I look forward to visiting again and bringing my fur babies.
Guest favourite
Apartment in Springfield
4.94 out of 5 average rating, 239 reviews

Quaint and Cozy Historic Hideaway

MelindaRating, 5 stars2 weeks ago
Great place !! I loved our stay. It was cozy ! Would definitely stay there again 😊 Dawn was very responsive and resourceful.

Bed and breakfast rentals with breakfast

Superhost
Private room in St. Augustine
4.83 out of 5 average rating, 42 reviews

King&3 bunks-Priv Bath, low cleaning fee

JonRating, 5 stars4 months ago
Our family of 8 stayed here for one night on our way up north. We are very grateful that this family hostel still exists! This is right downtown in the historic district and so everything is very walkable. Jenny and crew make everything very hospitable with a game for the children to play when they check in, games in the tv room and pancakes made for everyone in the morning. :) Great for a family that wants to explore St Augustine.
Superhost
Private room in St. Augustine
5 out of 5 average rating, 9 reviews

Lookout Suite at Vilano Beach

EthanRating, 5 stars3 months ago
The Airbnb and location were wonderful! You cannot beat the views from the bedroom window, the private deck and crows nest. Being that there is a completely separate entrance to the unit the space feels incredibly private. The bed was very comfortable and it was very quiet. Additionally everything was very clean, shoutout to Leo the housekeeper who is awesome! I highly highly recommend this gem of a spot and would stay here again in the future.
Superhost
Hotel room in St. Augustine
5 out of 5 average rating, 3 reviews

Princess Margaret at the Bayfront Marin House

ThomasRating, 5 stars15 months ago
Stayed here to celebrate my wedding. Looked exactly like the pictures and Sandy was very responsive. She answered all questions and was extremely helpful. Room was very clean and bathroom was huge. Hotel staff was friendly and offered local recommendations for meals and other activities to do. The only problem is the lack of parking. There is a private parking lot around the corner from the hotel. It’s a bit of a walk. So I recommend trying to park in front of the hotel, you just have to pay. Besides the parking, would definitely stay again.
Superhost
Hotel room in St. Augustine

Bridge of Lions Room at the Bayfront Marin House

TonyRating, 5 stars74 months ago
What a great place to stay in St Augustine, absolutely top notch!
Private room in St. Augustine
4.88 out of 5 average rating, 114 reviews

Downtown"Grace Darling"Old Powder House Inn-B'fast

AmandaRating, 5 stars2 weeks ago
The old powder House Inn is one of the best places I’ve ever stayed in my life. Paige, the manager made us feel so welcome. The rooms were so clean and beautiful, Paige made muffins and they were amazing, They have complementary wine, water, soda, and Brandy. They put their heart and soul into this inn. I literally felt at home and I was so comfortable being here. It definitely has an amazing positive vibe and the staff kept up with us like we were family checking in and making sure we were having a good time. And the water actually gets hot in the shower. And stays hot. Had a lot of bed-and-breakfast and Airbnb‘s. I’ve had the problem of the water not getting hot and taking uncomfortable showers, but the water pressure is amazing and it stays hot. They have humidifiers in the room and AC units and it was just an overall very comfortable stay I recommend this to anyone who comes to Saint Augustine.
Hotel room in St. Augustine
4.7 out of 5 average rating, 44 reviews

Romantic Jacuzzi spa-tub for two! Best location in the historic district!

WadeRating, 5 stars6 months ago
The only way to experience the night of lights is to get a room on Spanish street. This inn has a placement to the downtown available only to a small handful of properties.
Superhost
Hotel room in Lincolnville
4.8 out of 5 average rating, 20 reviews

Queen Spa Suite at the elegant Peace & Plenty Inn

EliRating, 5 stars1 week ago
Great spot really close to the historical center
Superhost
Private room in St. Augustine
5 out of 5 average rating, 21 reviews

Robinson Lewis at the Bayfront Marin House

LaurenRating, 5 stars1 month ago
Wonderful little gem in St Augustine. Attached to a bed and breakfast and super easy to find and wonderful commutation. Happy hour and breakfast was a huge bonus!

Quick stats about holiday rentals with breakfast included in Southside, Jacksonville

  • Total rentals

    30 properties

  • Nightly prices starting at

    $66 NZD before taxes and fees

  • Total number of reviews

    720 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Duval County
  5. Jacksonville
  6. Southside
  7. Rentals with breakfast