Vacation rentals with breakfast in Southside, Jacksonville

4.98 out of 5 average rating, 265 reviews

The exterior of a renovated bungalow is presented, featuring a light green facade and a welcoming front porch. A concrete driveway leads up to the house, with landscaped areas showcasing blooming flowers and trees, providing a calm and inviting appearance.

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!

Superhost

Home in Southeast Jacksonville

5 out of 5 average rating, 3 reviews

NEW!Private Modern Mandarin Horse farm-Events,Dogs

Nestled in historic Mandarin amongst birds and mature trees is our ultra private, elegant ranchette exuding style, comfort & tranquility. Soak in hot tub or relax under the 🌟.Corporate specials, certain dogs breeds for fee EVENTS with Fee for weddings,reunions,etc. Need two kings? Add guests for fee. Convenient to I-295, dining, shops, museums, parks, and river. Bring your RV/boat with permission,marina 1 mile. Inside find large 4K TVs,coffee/tea bar all well stocked!Holidays 3 night minimum.

4.98 out of 5 average rating, 266 reviews

Two bicycles are parked against a wall on a concrete slab, showcasing a light blue frame on one and a darker frame on the other. A phone holder and drink holder are attached to the handlebars of one bike, while the entrance to the home is visible in the background.

Home in Riverside

King bed home w/bikes on the best Riverside block!

This super fun house is perfectly located in Riverside; Jacksonville's most fun neighborhood. You can walk to bars, restaurants, yoga studios, shops, and more. We'll also send you a link to our personal G00gle doc with local tips for things to do, where to shop, and where to eat/drink. Our backyard has a firepit with adirondack chairs, a grill, and even 'smores kits. Plus, we have two bikes that you can use to cruise the neighborhood! The bikes even have cell phone holders & drink holders.

4.87 out of 5 average rating, 134 reviews

St. Augustine's Sea Pearl~ BEACH HOUSE ~ Sleeps 10

Ready to Experience Fun & Romance? Vacationers - no party? We love you guys, too! No Extra Fees if 10 people or under. EVENTS/PARTIES & WEDDINGS ~ ALL INCLUSIVES See YOUR PROPERTY for $ PRICING $ All Decor Included in your colors/style 100K in Decor (<: Ask about Payment Plans SeaSide Bar & Grill ~ Indoor Tiki Bar ~ 4 Bedrooms ~ Sleeps 10 Beach Ceremony ~ Beachside Dining for 50 ~ Dinner Garden Seats 150 people. Bridal Dressing Room ~ Hosting Beautiful Weddings is Our Super Power

Apartment in Southwest Jacksonville

A decorative pillow featuring a design of starfish rests on a lightly upholstered chair. The pillow has a soft white background with pale blue accents and coral piping, adding a touch of coastal decor to the seating area.

4.96 out of 5 average rating, 142 reviews

Val's Sanctuary. In-law-suite, private unit.

Take it easy at this unique and tranquil getaway with private entrance. Enjoy this peaceful rural country area on the screened porch with an evening tea. You can play some games or puzzles if you want to stay inside or Crochet on the front lawn to enjoy some fresh air & sunshine. We are 2.5 Miles from the WW Ranch Motorcross park. We don't have anything new but I can assure you it will be clean. Sorry we are not suited for children or pets, 2 guests Max. and check-in must be before 9PM.

Apartment in St. Augustine

Two bicycles are parked side by side, with a purple bike in the foreground and a black bike behind it. A window with horizontal blinds is visible in the background, allowing natural light to enter the space.

4.97 out of 5 average rating, 191 reviews

Charming Sanchez 2 ~ 5min drive to downtown/Bikes

20% OFF for first two guests that book in August! Can not be combined with any other offers! ——————————————- Newly renovated downstairs unit located just steps to uptown shopping/restaurants and a short drive to the main drag of historic downtown. Catch a trolley that will take you to 24 stops throughout downtown or enjoy a 15-20min stroll to downtown St George St. where shopping and restaurants are plenty! You are also a short walk to the Fountain of Youth and the Old Jail! No car needed!

5 out of 5 average rating, 36 reviews

The exterior of a brick duplex is displayed, featuring two garage doors with green accents. The entry door to the unit is visible, framed by windows. Parking spaces are located in front, contributing to easy access.

Home in San Marco

Walkable in San Marco • King • Porch • Sunsets

Coffee on the Front Porch & Happy Hour Cocktails on the Back! Welcome to our charming bottom unit in the heart of San Marco! Just 2 blocks from the town square and a quick 3-minute walk to the St. John’s River, you’ll love the easy access to everything. Relax on the front and back covered porches, play pool, or watch shows on the smart TVs. We’ve got outdoor seating, bikes, a comfy king bed, a fully stocked kitchen, fast WiFi, and a dedicated office—perfect for work or downtime.

Apartment in Southeast Jacksonville

The kitchenette features sleek black appliances and modern cabinetry against a white brick wall. A compact sink is positioned under a stylish faucet, with a small dish drying rack nearby. Natural light filters through a row of frosted glass block windows, illuminating the countertop.

5 out of 5 average rating, 100 reviews

The Cozy Basement in San Marco

Make yourself at home in this studio-style apartment located in a quiet neighborhood with a kitchenette and full bathroom that features modern updates. Centrally located, less than 5 minutes from historic downtown San Marco with trendy restaurants and shopping, just minutes away from all the shops and nightlife in the village square. Less than 15 minutes to Riverside and downtown Jacksonville including multiple hospitals. Also only 30 minutes from the airport and beaches.

4.97 out of 5 average rating, 77 reviews

A spacious lobby welcomes guests with high wooden ceilings and stone accents. Comfortable blue seating is arranged around wooden coffee tables, complemented by decorative plants. Natural light fills the area through large windows, creating an inviting environment for relaxation.

Condo in St. Augustine

Luxury Golf & Spa condo in Beautiful St. Augustine

Beautiful 1 bedroom pristine condo unit has it all. Comfortable king size bed, privacy, full bathroom with roman bathtub, washer/dryer, full kitchen with all the utensils you will need, two flat screen tv's, fast free wifi, private balcony overlooking lush gardens with a fountain. The Laterra resort boasts a plethora of amenities right outside your doorstep. Heated pool, pool with waterfall feature, hot tub, tennis courts, award winning Golf and restaurants nearby!

Home in Southwest Jacksonville

5 out of 5 average rating, 26 reviews

Cottontail Manor Ortega 4BR across from River

Welcome to the Cottontail Manor! Indulge in this luxurious large, serene space. Beautifully appointed 1 story (open floor plan) on one of the most desirable streets in Jax across from Ortega River & very close to Timuquana CC/Riverside/Avondale. Great for large family & special gatherings, or for those just wanting to get away and enjoy each other. A gift basket, spa robes & special coffees/tea await you! Extra comfortable beds with organic linens and soaps.

4.97 out of 5 average rating, 78 reviews

Guest suite in Beaches

Suite Nest @ The Beach

Popular by demand, Ive created another Suite Nest @The Beach! Only 4 blocks from the beach 🏝️& tennis courts, that you can see from the home! This is a Perfect Serene Suite for relaxation! With your own unique, private entrance, you never have to worry about privacy! This quiet, safe neighborhood on the south side of Jax Beach, 7 minutes to Mayo! I also have a golf cart for rent too! We have added a BBQ and outdoor patio furniture too!

A wooden deck features two adirondack chairs and a small table, illuminated by soft string lights above. A wooden fence surrounds the area, creating a private outdoor space that is bordered by trees in the background.

4.97 out of 5 average rating, 68 reviews

Coastal St. Augustine Retreat, Quiet Neighborhood

Family Amenity tailored experience on a quiet street with a comfortable front porch and back deck relaxing setting and only minutes to most major attractions! Only 7 minutes drive to downtown St. Augustine and minutes to the beach. - New home built in 2023, all new appliances and fresh interior - Corn Hole Set - Back porch string lights - 55 inch Smart TV - King Bed, Queen Bed, and 2 Twin Beds

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Popular amenities for Southside, Jacksonville breakfast rentals

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House rentals with breakfast

A bright and inviting living area features a ceiling fan and a large flat-screen television mounted above a modern fireplace. Two comfortable chairs and a neutral-toned sofa are arranged around a wooden coffee table, set on a light-colored area rug with subtle stripes.

4.84 out of 5 average rating, 49 reviews

Beach House w/hot tub &firepit-1 block from beach!

4.88 out of 5 average rating, 74 reviews

A living room with red walls features two floral-patterned sofas facing each other. A wooden coffee table sits in the center, and a small desk with a chair is positioned beside a window with light curtains. Soft light fills the space, creating a cozy ambiance.

Home in Murray Hill

Colorful Bungalow Sleeps 6 - Pet Friendly!

An outdoor area features a grassy lawn with a corn hole game and an inviting stone fire pit. Adirondack chairs surround the fire pit, and a gazebo with string lights can be seen in the background, enhancing the space's relaxing atmosphere.

5 out of 5 average rating, 57 reviews

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

4.8 out of 5 average rating, 94 reviews

A welcoming exterior view of the property is highlighted by soft lighting and lush greenery. The driveway accommodates a vehicle, while a screened porch is visible, offering a comfortable entrance. Surrounding trees and landscaping evoke a tropical ambiance, enhancing the inviting atmosphere.

Home in Jacksonville

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

A well-maintained exterior of a manufactured home features a welcoming entrance with wooden steps leading to the front door. Potted flowers adorn the entryway, while windows are framed by dark shutters, enhancing the inviting appearance of the home.

4.98 out of 5 average rating, 49 reviews

Twin Oaks Family Retreat, Sleeps 8, N St Augustine

A private pool is set within a fenced yard, featuring a distinctive shape and clear blue water. Surrounding the pool are neatly arranged potted plants and a well-maintained grassy area, all against a backdrop of a sunny sky with scattered clouds.

Home in Orange Park

4.82 out of 5 average rating, 178 reviews

Immaculate Home with Private Pool and Patio

The living room is characterized by neutral-toned furniture, featuring a pair of sofas adorned with blue and patterned cushions. Large windows provide views of the outdoors, while natural light brightens the space. A coffee table sits on a light area rug, enhancing the room's inviting atmosphere.

Home in Jacksonville

5 out of 5 average rating, 13 reviews

River House

4.98 out of 5 average rating, 57 reviews

A view of a sandy beach with a lifeguard chair prominently displayed in red. Gentle waves lap at the shore, and a fishing pier extends into the distance, framed by a backdrop of cloudy skies. Grasses are visible in the foreground, adding texture to the scene.

Home in Beaches

La Casa de la Mantaraya

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Apartment rentals with breakfast

A private balcony offers two comfortable rocking chairs, overlooking historic St. George Street. Warm sunlight filters in, creating a peaceful setting. The view captures charming buildings and cobblestone streets, enhancing the inviting ambiance of this central oasis.

Apartment in St. Augustine

4.79 out of 5 average rating, 19 reviews

Heart of St. Augustine Suite w/ Balcony, Parking &

The living area features a modern light fixture and a large television on a white entertainment unit. A comfortable chair is positioned nearby, with a potted plant adding a touch of greenery. Natural light filters through the windows, enhancing the inviting ambiance.

Apartment in San Marco

4.93 out of 5 average rating, 15 reviews

Oasis in Historic San Marco

4.96 out of 5 average rating, 291 reviews

A living area is highlighted by two plush seating arrangements, featuring a light-colored sofa and two deep burgundy chairs. A round coffee table sits atop a patterned area rug, while large windows invite natural light, enhancing the warm wood accents and the original fireplace.

Apartment in Springfield

Historic Rustic Glam Abode